Azo dye.



mansrarns PATENT. OFF

'ZEAD'LUULIUS,AND ERNST lrus'snnneenn, or LUDWIGSHAFEN-ON-THE-RHINE,GER- eEBmN A coaro mr o GERMANY- 9353741; In, Drawing.

Specification of Letters 1atent.

Beit known that we, 'PA1iL JULrUs and ERNST" FnssENneenR, doctors ofphilosophy and chemists, subjects. of the Emperor ofAustria-Hnngarygesidmg at Ludwigshafenon-the Rhine, Germany, haveinvented new and useful Improvements in Azo Dyes, of which the-followingis a. specification.

Our inventionirelatesto new azo coloring Ellljmatter's.

' We have discovered that by diazotizing3echlor-2-amino-l-metnylebenzene-o-sulfonic acid. and I combining thedime compound 7 with 2-naphthol, or with asulfonic-acid of- I- ;2-naphth'ol,- new azo coloring matters can be obtained'whieh areparticularly valuable on account of their great fastness against theaction of light.

The '3 chlor-2-amino-l methyl benzene 5- idsulfoni'c acid used accordingto this inven- 'tion is new and'can be obtained by treating 1-acid'yl-.amino-l-methyl-benzene-5-sulfonic acid :with chl'orin inaqueous solution and jthensplittingofi? the'acidyl group from the25.1pr0d110t so obtained.

The new coloring matters obtainable acoording'toour invention arecharacterized by their sodium salts being soluble in Water,

their bariuin'salts are insoluble in water;

When dry, they consist of orange powders,

in the-form oftheir lakes they possess yellow to orange shades, and uponreduction with tin and hydrochloric acid they yield 3-chlor- 2 amino 1-methyl -benzene 5 sulfonic acid and a 1,2 amino-naphthol body. The new,coloi'ing mattei" which We WlSh'tO be under-- stood as claimingspecifically is that obtainableby combining the aforesaid diazo compoundwith 2-naphtliol. It yields orange 40 lakes, and upon reduction with tinand hydrochloric acid it gives rise to 3-chlor-2- amino-l-methyl-benzene-5-sulfonic acid and 1-amino-2-naphthol. 'Thefollowingexample will serve to illustrate further the nature of our invention and.how it can be carried intopractical effeet, but the invention is notconfined to this example. The parts are by Weight. Diazotize twenty-two.and one-fifthparts of 5 0 3-chlor-2-amino-1-methyl-benzene-5-sulfonicacid in the usual manner and allow the dia o compound to run, whilestirring, into a solutlon of fifteenparts of beta-naphthol, to

which sufficient sodium carbonate has been added to maintain the wholealkaline.

yellowish orange 1. The coloring matters which can be ob-' I tained from3-chlor-2-amino-I-methyl-benzene-5-sulfonic acid and a hereinbefore de-'fined Q-naphthol body, which coloring matters consist in the dry stateof orange powders,.their sodium salts are soluble in Water, their bariumsalts are insoluble in Water, in the form of their lakes they possessorange shades, and upon reduction 'with tin and hydrochloric acid theygive rise to 3-chlor-2- amino-l-methyl-benzene-5-sulfonic acid and al2-amino-naphthol body,

2. The coloring matter Which can be obtained by combining diazotized3-chlor-2- amino-l-inethyl-benzene-5-sulfonic acid with 2-naphthol,which coloring matter consists when dry of an orange powder, its sodiumsalt is soluble in Water, its barium salt is ing Patented Sept. 28,1909; Application filed June 22, 1909. Serial No, 563,634. V

obtained. In a assiienons'ronnmscnn AN 1LI N& SODA EABRIK, onLUDWIGSHAFEN-ON- soluble in water, in the form of its lakes it,"

possesses orange shades, and upon reduction PAUL JULIUS. ERNSTFUSSENEGGER.

Witnesses: ERNEST G. EHmIAnnr,

J. Arno. LLOYD.

